


Oneupmanship

by twinsarein



Category: Supernatural
Genre: M/M
Language: English
Status: Completed
Published: 2011-05-10
Updated: 2011-05-10
Packaged: 2017-10-19 08:11:38
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 1,044
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/198760
Author URL: https://archiveofourown.org/users/twinsarein/pseuds/twinsarein
Summary: <blockquote class="userstuff">
              <p>Some side-by-side masturbation in the backseat of the Impala.</p>
            </blockquote>





	Oneupmanship

Sam shifted around under the blanket, and Dean thought he was just trying to get more comfortable. Both of them were kind of listing towards each other, with Sam’s head on Dean’s shoulder, and Dean resting his head on Sam’s. As they got older, the backseat of the Impala became more and more crowded.

Except, the movement under the blanket didn’t stop, although it did change from a shifting of Sam’s whole body, to just one of his arms. Dean’s eyes widen when he realized what Sammy was doing. “Jeez, Sammy, I’m not playing this game with you anymore. I’m eighteen, now - a man, not a kid.”

Dean quickly glanced at their father in the front seat, but with the music blaring and his window open, there was no way he could hear Dean’s whispering.

“C’mon, Dean. Do it with me. I bet I can finally last longer than you.”

A soft snort expressed Dean’s opinion of that assertion very well, he thought. He should have known better. Sam was nothing if not persistent, after all.

“What are you afraid of? That your little brother can finally best you at something?”

Even knowing what his brother was doing, Dean was still unable to resist the challenge. He shifted around under the blanket, and slid his zipper down quietly. “It is so on, little brother. Loser does the laundry for a week.”

Gripping his already hardening dick, Dean started jacking himself right away. There were rules after all; rules that had to be followed once you’d accepted a challenge. Can’t stop once you’ve started. Can’t take it slow. Each of them has to try their best to make themselves come. They also can’t touch each other below the waist, but they can do whatever else it takes to make the other one come first. Whoever came first, loses.

“Mmmm, it feels so good, Dean. I like it best when I’m holding on really tight, and have to really work hard to get my hand to slide up and down my dick.”

With Sammy’s head resting on his shoulder, Dean thought the kid had an unfair advantage - being able to talk right into Dean’s ear like that, puffs of breath brushing his earlobe, making him shiver. Well, two could play at that game. “That does sound good, but I prefer to slide into some girl’s tight pussy. So much better than a hand. There’s no way I could describe how good the wet heat feels as it closes around your dick.”

The soft sound that escaped Sam’s throat was Dean’s victory, as was the wetter sound of Sam’s hand on his dick. Sammy was leaking precome. Dean had to strain to hear over the wind of their father’s open window and the music blaring from the tape deck, but Dean was used to tuning into his brother.

For instance, he could hear his brother’s breathing speeding up. He figured this victory was in the bag, but his brother surprised him. “I’ve h-heard there’s something even tighter, maybe hotter, t-too.”

“Yeah? What’s that, Sammy?”

“Fucking into someone’s ass. Pushing in until your balls are slapping against butt cheeks.”

Dean knew a little about gay sex, but he hadn’t expected Sam to know about it. The thought that he did, and the filthy words coming out of his mouth almost made Dean lose it. He managed to hold on by the skin of his teeth.

Things low down in Dean’s belly were clenching up, and he knew his orgasm wasn’t far off, so he had to do something soon. Upping the stakes was one thing he was very good at, however.

“Yeah, it’s true Sammy. Getting to fuck someone’s ass is the best, it almost feels as though your dick is in a vise, because until they relax they are clenching so hard around you. Even better is that special spot that every man has deep inside them, though. You get someone to touch that, and your mind will melt from the pleasure.”

Shifting position, Dean manages to be the one with his mouth near Sammy’s ear. “You can touch yourself down there, Sammy. Just rub over your hole, and it’ll feel so good, but only a fraction of how good it’ll feel if you get that spot inside touched. Do it, Sammy. Lick your finger and then rub it over your hole. C’mon, do it!”

A small hand emerged from the blanket, and again Dean thought he was about to come when he saw Sam sucking on a finger, and then rolling his eyes back to try and see Dean as he pushed it under the blanket.

Sam pushed his face into Dean’s neck, and panted against his skin, making Dean shiver again. Sam’s noises picked up, and Dean could feel his own orgasm building, his balls drawing up as he listened. “Feels good, doesn’t it, Sammy? Imagine pushing that finger inside, being able to reach that spot, stroking over it.”

Sam pressed his face harder against Dean’s neck, and Dean felt more than heard the moan as his brother jerked against him. Not a moment too soon, as Dean’s own orgasm flashed through his body, burning like lightning in reverse, leaving him gasping.

They slumped against each other, shivering in reaction. Still breathless, Sam pulled back from Dean’s neck. “I-I almost beat you. A few more seconds...”

The pleasure from the orgasm still flowing through him, Dean had to force himself to respond to that challenge to his win. “In your dreams, little bro. I could have held on longer; I just decided not to bother.” Not exactly a lie, just a creative reinterpretation. No need for Sammy to know that, though. “I’ve got four year’s on you, Sammy. There is no way you can match my stamina.”

Sam brought his come covered hand out of the blanket, and licked it clean. “Someday soon I will, Dean. You just watch and wait.”

Dean felt his dick give another twitch, and he closed his eyes to block out the sight. Sammy might be several years younger, and way less experienced than him, but he obviously had good instincts. Dean would never say it aloud, but he thought Sam was right. It was just a matter of time.


End file.
